The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans
Mellor, J. M. and El-Sagheer, A. H. (2000) The importance of A-strain in the stereochemical control of ring opening of tetrahydropyrans. Tetrahedron Letters, 41, (38), 7387-7390. (doi:10.1016/S0040-4039(00)01256-9).
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Original Publication URL: http://dx.doi.org/10.1016/S0040-4039(00)01256-9
Description/Abstract
Readily available cyclic beta-alkoxy-alpha,beta-unsaturated trifluoromethylketones react with excess phenyl magnesium bromide by initial 1,4-addition, followed by ring opening to give a variety of products. Both the major products, unsaturated diols, and the minor products, as shown by X-ray diffraction studies, are generated with high stereoselectivity, which is attributed to A(1,3)-strain.
| Item Type: | Article |
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| Related URLs: | |
| Keywords: | allylic strain, grignard reagents, tetrahydropyrans diastereoselective synthesis, allylic 1,3-strain, epoxidation |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 19005 |
| Date Deposited: | 15 Dec 2005 |
| Last Modified: | 01 Jun 2011 16:07 |
| Contributors: | Mellor, J. M. (Author) El-Sagheer, A. H. (Author) |
| Date: | 16 September 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/19005 |
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